Today, Lorie Jones sits down with Rebecca Callahan, founder of Summer Day, whose career journey spans nearly three decades in corporate travel and hospitality before pivoting to women’s leadership development.
Rebecca is on a mission to help women install confidence earlier in their careers, aiming to close the confidence gap that holds so many back in their 20s and 30s. She reveals her career-defining moments and discusses creating real balance and the power of authentic self-advocacy.
Whether you’re a young professional or navigating the mid-career maze, this conversation offers honest insights and actionable advice to inspire you to take your seat at the table and claim your voice—even sooner than you think you’re ready. Join us and discover how you can start being fearless today.
Show Highlights:
- How going with the flow can land you the right passion pivot. [06:21]
- Support for women experiencing an early/mid-career confidence gap. [08:23]
- Discover 3 key investments for aspiring women leaders. [12:25]
- Why it’s so important to communicate career dissatisfaction. [16:25]
- The value of making sure not to leave a job on bad terms. [20:32]
- Should you buy stocks when the market’s unpredictable? [22:48]
- How to finesse the energy of having a “too much” personality. [26:50]
- Explore roleplaying as a way to nail tough conversations. [30:52]
- Sealing success by aligning motherhood, choices, and non-negotiables. [32:31]
- The power of asking for help. [39:02]
Connect with Rebecca Callahan, find her on LinkedIn at https://www.linkedin.com/in/rebeccacallahan, or visit her website https://www.summerday-llc.com/about.
You can also reach Rebecca via at rebecca@summerday-llc.com.
If you enjoyed this episode, please go to Apple Podcasts and leave a review!
For more information about Lorie Jones, go to https://fearlessfinancialadvisors.com/fearless-females.
00:00.93
Lorie Jones
Good morning, fearless females. So today we have Rebecca Callahan with us. She is the founder of Summer Day. And I’ve had a couple of opportunities just to chat with Rebecca. I really think this is going to be a good, insightful show where she helps us out with a lot of different ideas. So thank you so much for doing this, Rebecca. i appreciate it.
00:20.93
Rebecca Callahan
Thank you for having me. I’m really excited to chat.
00:24.05
Lorie Jones
So my first question is always my favorite. I’m a reader. I love reading. My book list is too long to get through this year and probably verging on into next year by this point. And I still keep asking, what is your favorite book?
00:38.84
Rebecca Callahan
So I’m the same way. My, my list is ridiculous. I don’t know that I’m going have enough time in my life to read all all of the books, but po So that’s actually a hard question. I’ve actually been thinking about that. um I want to say that my favorite book of all times is Atlas Shrugged by Ayn Rand.
01:01.14
Rebecca Callahan
And I probably read it about once every 10, 15 years, because it’s like this big and it takes forever to get through. And every time I read it or reread it, I learn something new.
01:13.05
Lorie Jones
So what, what, what speaks to you in that book? Like, why, why do you like it so much?
01:18.12
Rebecca Callahan
Honestly, it was probably the first book that I read that was very, there is a female antagonist and she was a you know, a master of industry.
01:30.51
Rebecca Callahan
Dagny Tiger was the original fearless female, to be honest.
01:36.28
Lorie Jones
Yeah. And as we’re going through Women’s History Month, to have a ah great um female leader in in literature or business or pretty much anywhere is kind of exciting.
01:43.41
Rebecca Callahan
Yeah.
01:47.70
Lorie Jones
it It does. That speaks to me. So I love that.
01:52.10
Rebecca Callahan
Well, right. And it’s also, um, you know, Ayn Rand lived in Russia and she moved to the U S and so she lived, um, without capitalism for so long in her life. And when she, you know, she like, that’s what Atlas shrugged and, um, oh gosh, what’s the other one that she wrote? Um, Fountainhead are her two big ones. And it’s just very much about,
02:18.58
Rebecca Callahan
um how how good capitalism is and of course know you can go too far on capitalism but the way that she approached it just competition competition is good and all of those different things it was just that’s really from a corporate perspective that’s in my mind that’s how corporate should be run and then to have it from a female from a woman’s perspective is just you know icing on the top
02:24.66
Lorie Jones
Mm-hmm.
02:43.53
Lorie Jones
Yeah, that’s interesting. I have read both of hers, but I’ll have to go back. I’ll have to put them on my list and read them again. so Because it’s been a while. it has been.
02:52.94
Rebecca Callahan
Yeah.
02:53.50
Lorie Jones
and So tell me just a little bit about your journey, Rebecca.
02:53.78
Rebecca Callahan
Yeah.
02:56.78
Lorie Jones
Where did you get started? Did you always know what you wanted to do How did you flow through that journey? And what are you doing now?
03:03.90
Rebecca Callahan
Yeah. So, no, I did not always know what I wanted to do. I probably don’t know what I want to do right now. So, um, the flow is definitely something that I have gone with most of my career, but I was,
03:17.91
Rebecca Callahan
oh gosh I gotta tell you, I used to say that I was 20 years in corporate, 20 plus years in corporate. And when I actually looked at the numbers, it’s more like 30 years. so I’m almost 30 years in corporate. i did most of my career in travel and hospitality. And i you know, I had a lot of different jobs in different roles, especially as I, you know, kept getting promoted and getting on leadership teams and all of those different things.
03:48.28
Rebecca Callahan
So I dabbled in marketing and account management and operations and process improvement and sales sales up. kind of touched a whole lot of different things for a lot of different industries, but the through line of my career has always been kind of post sales account management.
04:05.87
Rebecca Callahan
So once somebody comes in the door, how do we keep them? And how do we grow them? So that’s really been my focus, regardless of what my actual role in title was, that’s really been my focus is kind of building those relationships ongoing.
04:11.53
Lorie Jones
Thank you.
04:22.14
Rebecca Callahan
About five years ago, I did a passion pivot from travel and hospitality into leadership development. Um, I actually started working for a company that ran women’s leadership development programs and workshops. And I built a, an alumni community for them for the same reason to keep those women that have gone through the workshops close, um, and keep them engaged and learning. And I did a lot of networking and a lot of continuing education for them.
04:52.73
Rebecca Callahan
Loved it. So when I decided it was time to go off on my own, um, which was about two years ago, it was really, um very easy from a go with the flow perspective to go into coaching. and so I am. a certified coach. Now I’ve been a certified coach for a couple of years. I focus in almost entirely on early and mid career women. And the big thing that I’m doing right now is I’m building and running peer advisory boards for early and mid career women. It’s this beautiful, um, mix of the community building that I love to do and the coaching and all in service of those next generation of leaders that are going to come up coming up behind us.
05:40.25
Lorie Jones
Yeah, we had a chance to just chat about this, ah you know, a couple weeks ago, and I loved your emphasis on early career and, you know, mid-career, but but i was I was really loving the early career women um because it it
05:54.25
Rebecca Callahan
Yeah.
05:56.06
Lorie Jones
It kind of that’s they’re enthusiastic, they’re gung they are so full of energy, but they might not have the experience that they’re going to have later on in their career.
05:59.22
Rebecca Callahan
Yes.
06:07.00
Rebecca Callahan
Yeah.
06:08.75
Lorie Jones
And I love that you’re helping and mentoring them um through those early stages. Not a lot of people focus on that stage. And I love that you do.
06:16.79
Rebecca Callahan
No, there’s there’s a big gap. I mean, when you graduate from college, you know there’s a lot of support, alumni networks and in college career services and all of that. and then when you get to like VP level, there’s a lot of stuff there’s, um, you know, chief and pavilion and this day, I mean, there’s so many opportunities once you get to that, but there’s not a lot in the middle and what I’ve come to realize working with clients and talking to women, um, at that stage is it honestly, it comes down to, um, confidence and,
06:53.46
Rebecca Callahan
younger women don’t necessarily have a whole lot of confidence in themselves, in their voice, in what they want to do in the ability to make mistakes and the ability to stand up for themselves, to ask for what they want to advocate.
07:06.34
Rebecca Callahan
And I i mean, I didn’t, I don’t know if you did, but I, I mean, when i was in my twenties and thirties, even into my forties, there’s no way i have it now, but it took me almost 30 years to get there.
07:14.62
Lorie Jones
Yeah. Mm-hmm. Mm-hmm.
07:18.82
Rebecca Callahan
And my the The underlying thing, root of everything that I’m doing right now is how do I help women instill that confidence in themselves and each other earlier?
07:31.58
Rebecca Callahan
Because if you can do it earlier, your career, your life, how you show up, everything is going to benefit from that. So that’s, yeah, I love working with early career women and mid-career women because of that, because there’s so much opportunity.
07:46.98
Lorie Jones
Oh, yeah. There’s a lot. um There’s a lot. There’s a lot of places you can go from there. And I i love the I was telling a guest earlier today, I love the the enthusiasm that they come with, like the their ability to question.
08:01.11
Rebecca Callahan
Yeah. Yeah.
08:03.12
Lorie Jones
And and I do think it gets quashed sometimes in those early stages of their career. And I wish it didn’t like I wish that the Hopefully that’s what you’re doing is helping it not to get questioned because I think that they’re engaged.
08:21.94
Lorie Jones
They’re so ready to, to be a part of the, the, um, the companies and just push them forward.
08:30.63
Rebecca Callahan
I agree. And actually, um i mean, just as an example, and this was, oh my gosh, I guess at this point, it was probably 10 years ago. I had um a a woman that was working for me um that I was trying to promote from a um hourly to salary. And in my head, like i she she initially said no when I tried to